DIASTEREOSELECTIVE SYNTHESIS OF THE KEY INTERMEDIATE OF THE BO-2727 SIDE-CHAIN

Authors
OHTAKE N JONA H OKADA S OKAMOTO O IMAI Y USHIJIMA R NAKAGAWA S
Citation
N. Ohtake et al., DIASTEREOSELECTIVE SYNTHESIS OF THE KEY INTERMEDIATE OF THE BO-2727 SIDE-CHAIN, Tetrahedron : asymmetry, 8(17), 1997, pp. 2939-2947
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
17
Year of publication
1997
Pages
2939 - 2947
Database
ISI
SICI code
0957-4166(1997)8:17<2939:DSOTKI>2.0.ZU;2-J
Abstract
The key intermediate of the BO-2727 side chain 3 was prepared diastere oselectively by two alternative methods: via the aldol reaction of (2S ,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalyt ic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalys t (98% de). (C) 1997 Elsevier Science Ltd.